cimetidine   Click here for help

GtoPdb Ligand ID: 1231

Synonyms: cimetidine HCl | Tagamet®
Approved drug PDB Ligand
cimetidine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Cimetidine is a histamine H2 receptor antagonist.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: cimetidine

cimetidine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 114.19
Molecular weight 252.12
XLogP 1.02
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES N#CNC(=NC)NCCSCc1nc[nH]c1C
Isomeric SMILES N#CNC(=NC)NCCSCc1nc[nH]c1C
InChI InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
InChI Key AQIXAKUUQRKLND-UHFFFAOYSA-N
References
1. Beukers MW, Klaassen CH, De Grip WJ, Verzijl D, Timmerman H, Leurs R. (1997)
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.
Br J Pharmacol, 122 (5): 867-74. [PMID:9384502]
2. Cappelli A, Manini M, Valenti S, Castriconi F, Giuliani G, Anzini M, Brogi S, Butini S, Gemma S, Campiani G et al.. (2013)
Synthesis and structure-activity relationship studies in serotonin 5-HT1A receptor agonists based on fused pyrrolidone scaffolds.
Eur J Med Chem, 63: 85-94. [PMID:23466604]
3. Engel K, Wang J. (2005)
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
Mol Pharmacol, 68 (5): 1397-407. [PMID:16099839]
4. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H. (1999)
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
J Biol Chem, 274 (19): 13675-80. [PMID:10224140]
5. Masuda S, Terada T, Yonezawa A, Tanihara Y, Kishimoto K, Katsura T, Ogawa O, Inui K. (2006)
Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2.
J Am Soc Nephrol, 17 (8): 2127-35. [PMID:16807400]
6. Ohta KY, Inoue K, Hayashi Y, Yuasa H. (2006)
Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney.
Drug Metab Dispos, 34 (11): 1868-74. [PMID:16928787]
7. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
8. Tsuda M, Terada T, Ueba M, Sato T, Masuda S, Katsura T, Inui K. (2009)
Involvement of human multidrug and toxin extrusion 1 in the drug interaction between cimetidine and metformin in renal epithelial cells.
J Pharmacol Exp Ther, 329 (1): 185-91. [PMID:19164462]
9. Wang J. (2016)
The plasma membrane monoamine transporter (PMAT): Structure, function, and role in organic cation disposition.
Clin Pharmacol Ther, 100 (5): 489-499. [PMID:27506881]